Apartment vacation rentals in South Loop, Chicago

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Top-rated apartment rentals in South Loop, Chicago

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Guest favorite

Apartment in Lincoln Park

4.98 out of 5 average rating, 298 reviews

Redesigned Lower Level Studio in Historic Building

The space is very comfortable, quiet and cozy. There are new cabinets, granite counter tops, all new appliances and a washer and dryer. Guests sleep on a king size tempur-pedic mattress or a queen size trundle style pull out sofa. There is hi-speed wi-fi, cable TV (Showtime), 55' flat screen TV and a wood burning fireplace. The bathroom is immaculate and includes a full bathtub with shower. This is a private apartment and you will have access to the entire suite. There is a back and front door with adequate lighting and easy access for guests. My family and I live next door and I will be available at our guests convenience. I am happy to provide any information, recommendations, directions etc.. I am easy to reach and am always available but will not intrude on our guests privacy. This unit is on a beautiful tree lined street in the heart of Old Town, close to St. Michael's Church, Steppenwolf Theater, and the Second City Improv Theater. The location allows for easy access to all of Chicago by either train, bus, or car. The blue and brown line train stations are within walking distance. Street parking is readily available and no permits are necessary. A Chicago Cab or Uber can get you to Milleniumm Park in approx. 15 minutes. Four adults can comfortably stay in this unit. The king size tempur_pedic mattress is the pinnacle of comfort and the queen size trundle style pull out sofa is comparable to sleeping on an actual queen size mattress. The queen size bed could comfortably fit 3 children. There is street parking readily available but I can provide an assigned space behind the building if necessary, for additional cost.

Oct 24 – 31

G$25,865 GYD per night

Guest favorite

Apartment in Humboldt Park

4.98 out of 5 average rating, 108 reviews

Humboldt Park Loft

Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Sep 15 – 22

G$25,527 GYD per night

Guest favorite

Apartment in Near South Side

4.87 out of 5 average rating, 156 reviews

Stunning Panoramic Chicago Views & Free Parking

Indulge in the epitome of luxury at our exceptional property with a host of amenities: 24-hour door attendant, heated parking, hot tub, modern workout and rec room, and stunning Chicago views. Situated in a secure, scenic South Loop neighborhood, our upscale abode grants swift access/steps to McCormick Place and Wintrust Arena. Discover the best of Chicago from this ideal spot, with easy public transport and airport commutes. Your remarkable experience begins in this lavish urban retreat!

Feb 2 – 9

G$84,178 GYD per night

Guest favorite

Apartment in West Town

4.96 out of 5 average rating, 263 reviews

Turquoise Wonder - Clean, Cozy & Stylish Apt

Clean, stylish & comfy apartment, perfect for 1 or 2 adults. 2 guest maximum, no children. Close to public transit (bus), wonderful restaurants & bars, gift shops, boutiques, coffee shops, parks, museums & more. Ukrainian Village/Humboldt Park area. King size comfortable Tempurpedic mattress. Central heat, A/C. Nice kitchen w/ stainless appliances, excellent bathroom, shower & tub. Free street parking. Relax in the comfort of the Turquoise Wonder! Enhanced cleaning protocols for COVID.

Nov 20 – 27

G$20,829 GYD per night

Guest favorite

Apartment in Chicago

4.94 out of 5 average rating, 265 reviews

Cozy City Living-Near Downtown-Train-Food!

Experience the best of one of Chicago's favorite neighborhoods in this recently renovated, modern 2BR apartment. Perfect for couples, families, or small groups. Centrally located, minutes to downtown, CTA/L Pink Line train one block away. Free WiFi, cable, parking, in-unit front load washer/dryer, fresh towels & linens. Explore the vibrant community, delicious restaurants, and cultural venues. Book now for a comfortable and memorable stay in the heart of Pilsen!

Sep 9 – 16

G$35,465 GYD per night

Superhost

Apartment in Pilsen Historic District

4.86 out of 5 average rating, 235 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond.

Oct 2 – 9

G$15,903 GYD per night

Guest favorite

Apartment in Chicago

4.98 out of 5 average rating, 132 reviews

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

Jul 23 – 30

G$30,819 GYD per night

Guest favorite

Apartment in Little Italy

4.98 out of 5 average rating, 199 reviews

Spacious 2BR on Quiet St - Free Park/Late Checkout

2 bedroom, 1 bathroom apartment, located just off Taylor Street in the heart Little Italy! Views of the Sears Tower from the front yard. Safe and lively neighborhood, packed with diverse restaurants, cafes, bakeries, parks, etc. all just a short walk from the apartment! Nearby West Loop also packed with trendy shops and amazing dining spots. Flat screen TV in every room, In-unit laundry, patio space, coffee/tea provided. 1pm check out!

Jan 9 – 16

G$36,989 GYD per night

Superhost

Apartment in Chicago

4.84 out of 5 average rating, 176 reviews

The Cottage

Nice cozy and welcoming place. Easy access to public transportation. 10 to 15 minutes from downtown, museums, Sox and Bulls stadiums. Located in the colorful and lively neighborhood of Pilsen and close to Little Italy. Smart devices installed for easy check-in and safety (extremely accurate and sensitive smoke detector warning all occupants of possible problems). Guest wifi included with some feel home amenities.

Oct 25 – Nov 1

G$15,895 GYD per night

Guest favorite

Apartment in Pilsen Historic District

4.89 out of 5 average rating, 243 reviews

Modern

Welcome to Pilsen, the neighborhood I have been living for 20 years! It is really cool and artsy. Forbes Magazine named the Pilsen neighborhood as one of the 12 coolest neighborhoods in the world. https://www.nbcchicago.com/blogs/worth-the-trip/Chicago-Neighborhood-Named-Among-Coolest-in-World-by-Forbes-486702851.html https://chicago.suntimes.com/news/pilsen-chicago-forbes-coolest-neighborhoods/

Oct 22 – 29

G$22,851 GYD per night

Guest favorite

Apartment in Bridgeport

4.98 out of 5 average rating, 171 reviews

Bridgeport Garden Apartment

Enjoy a peaceful stay at this colorful, creative, artsy and relaxing garden unit apartment in the heart of Bridgeport. Located a few blocks away from Bridgeport's best bars and restaurants. This unit is good for couples, solo adventurers, business travelers and families (with kids). Street parking is free, and I’m readily available via phone or in person (I live a few minutes away).

Sep 16 – 23

G$23,059 GYD per night

Guest favorite

Apartment in Near South Side

4.97 out of 5 average rating, 117 reviews

Sprawling South Loop 3Br/2Ba with parking

Conveniently located near McCormick Place and Soldier Field. Close to parks, shopping, and public transportation. Newly remodeled unit. Second floor unit with no elevator in building. Modern bathrooms and kitchen, new fixtures throughout, nice front deck, in-unit full-sized washer and dryer, hardwood floors throughout. One parking space included, but absolutely NO OVERSIZED VEHICLES

Jan 6 – 13

G$70,072 GYD per night